Thifensulfuron-methyl (Ref: DPX M6316)

Thifensulfuron-methyl (Ref: DPX M6316)	Last updated: 21/10/2020
(Also known as: thifensulfuron; thiameturon; M 6316; thifensulfuron ME)

GENERAL INFORMATION

Description

A post-emergence herbicide for the control of grass and broad-leaved weeds

Example pests controlled

Pigweed; Wild mustard; Lady's thumb; Lambsquarters; Velvetleaf; Bindweed; Chickweed; Cleavers; Knotgrass; Pansy; Poppy; Thistle

Example applications

Spring & Winter cereals including wheat, barley, triticale, rye, oats; Maize; Soybeans; Tomatoes

Efficacy & activity

Availability status

Current

Introduction & key dates

1985, first reported; 1988, first approvals

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/10/2031

UK LERAP status

Buffer probably required in UK - see product label

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

United Kingdom/Austria

Date EC 1107/2009 inclusion expires

31/10/2031

EU Candidate for substitution (CfS)

Listed in EU database

Yes

Approved for use (✓) under EC 1107/2009 in the following EU Member States

ATAustria	BEBelgium	BGBulgaria	CYCyprus	CZCzech Republic	DEGermany	DKDenmark	EEEstonia	ELGreece
✓	✓	✓		✓	✓	✓	✓	✓
ESSpain	FIFinland	FRFrance	HRCroatia	HUHungary	IEIreland	ITItaly	LTLithuania	LULuxembourg
✓	✓	✓	✓	✓	✓	✓	✓	✓
LVLatvia	MTMalta	NLNetherlands	PLPoland	PTPortugal	RORomania	SESweden	SISlovenia	SKSlovakia
✓		✓	✓	✓	✓	✓	✓	✓

Also used in

Australia

Chemical structure

Isomerism

Chemical formula

C₁₂H₁₃N₅O₆S₂

Canonical SMILES

CC1=NC(=NC(=N1)OC)NC(=O)NS(=O)(=O)C2=C(SC=C2)C(=O)OC

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

AHTPATJNIAFOLR-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C12H13N5O6S2/c1-6-13-10(16-12(14-6)23-3)15-11(19)17-25(20,21)7-4-5-24-8(7)9(18)22-2/h4-5H,1-3H3,(H2,13,14,15,16,17,19)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
thifensulfuron-methyl	-

General status

Pesticide type

Herbicide

Substance group

Sulfonylurea

Minimum active substance purity

979 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Selective, absorbed through folInhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS

CAS RN

79277-27-3

EC number

CIPAC number

452

US EPA chemical code

128845

PubChem CID

73674

Molecular mass

387.39

PIN (Preferred Identification Name)

methyl 3-{[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl]sulfamoyl}thiophene-2-carboxylate

IUPAC name

methyl 3-(4-methoxy-6-methyl-1,3,5-triazin-2-ylcarbamoylsulfamoyl)thiophene-2-carboxylate

CAS name

methyl 3-(((((4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino)carbonyl)amino)sulfonyl)-2-thiophenecarboxylate

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Herbicide Resistance Classification (WSSA)

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Amaranthus hybridus

Physical state

Fine white powder

Related substances & organisms

fluroxypyr

tribenuron-methyl

metsulfuron-methyl

thifensulfuron

Formulations

Property

Value

Example manufacturers & suppliers of products using this active now or historically

Lancer
Pennant
Pinnacle
Harmony M

Example products using this active

Cheminova
DuPont
Headland

Formulation and application details

Often supplied as water soluble granules that are mixed with water and used as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

54.1

Moderate

Solubility - In organic solvents at 20 °C (mg l⁻¹)

1900

Acetone

900

Ethanol

2600

Ethyl acetate

2600

Methanol

Melting point (°C)

171

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

162

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

Octanol-water partition coefficient at pH 7, 20 °C

2.24 X 10^-02

Calculated

Log P

-1.65

Low

Bulk density (g ml⁻¹)

1.49

Dissociation constant pKa) at 25 °C

4.0

Weak acid

Vapour pressure at 20 °C (mPa)

5.19 X 10^-06

Low volatility

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

3.25 X 10^-08

Non-volatile

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

Neutral solution: 233nm =26124
Acid solution: 224nm =18313, 250nm=13,520
Basic solution: 234nm =26505

Surface tension (mN m⁻¹)

63.8

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

1.39

Non-persistent

DT₅₀ (lab at 20 °C)

1.39

Non-persistent

DT₅₀ (field)

Non-persistent

DT₉₀ (lab at 20 °C)

Non-persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier 2014 lab studies DT₅₀ range 0.85-3.1 days, DT₉₀ range 5.7-8.6 days, field studies (pre 2014 data) DT₅₀ range 3-20 days, DT₉₀ range 10-66 days

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

11.0

Note

Field grown soybean, whole plant, n=1

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Stable

Note

pH sensitive: DT₅₀ 14.6 days at pH 5, 10 days at pH 9, mean of light and dark

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

180

Persistent

Note

pH sensitive: DT₅₀ 5 days at pH 5, 90 days at pH 9

Water-sediment DT₅₀ (days)

22.8

Fast

Water phase only DT₅₀ (days)

Slow

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

0.74

Mobile

K_oc

28.3

Notes and range

EU dossier pre 2014 K_d range 0.08-1.38 mL g⁻¹; K_oc range 13-55 mL g⁻¹, Soils =4

Freundlich

K_f

0.508

Very mobile

K_foc

9.0

¹/_n

0.932

Notes and range

EU dossier 2015 K_f range 0.09-2.55 mL g⁻¹, K_foc range 3.1-86 mL g⁻¹, ¹/_n range 0.821-1.01, soils=9

pH sensitivity

Possible trend showing higher adsorption on more acidic soils

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

3.05

Calculated

High leachability

SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate

Value

8.44 X 10^-02

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

thiophene sulfonamide (Ref: IN-W8268)

Soil

0.296

Major fraction, Relevant

thifensulfuron (Ref: IN-L9225)

Soil

0.940

Major fraction, Relevant

O-desmethylthifensulfuron methyl (Ref: IN-L9226)

Soil

0.185

Major fraction, Relevant

2-amino-4-methoxy-6-methyl-1,3,5-triazine (Ref: IN-A4098)

Soil

0.180

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

triazine urea (Ref: IN-V7160)
Note: Soil DT50=19.4 days; Kfoc=114 mL/g

a=Water; Soil; Sediment; Plants

a=0.25

O-desmethyl thifensulfuron acid (Ref: IN-JZ789)
Note: Soil DT50=60 days; Kfoc=31.1 mL/g

Soil; Water; Sediment

0.100

-
Note: Soil DT50=73 days; Koc=524 mL/g

2-acid-3-triuret

Soil; Water; Sediment

0.170

2-acid-3-sulfonamide (Ref: IN-9223)
Note: Soil DT50=178 days; Kfoc=4.07 mL/g

Soil; Water; Sediment; Plants; Animals

0.190

2-ester-3-sulfonamide (Ref: IN-A5546)
Note: Soil DT50= 3days; Kfoc=49 mL/g

Soil

0.105

methyl 3-(((((acetylamino)carbonylamino)carbonyl-amino)carbonylamino)sulfonyl)-2-thiophenecarboxylate (Ref: IN-RDF00)

2-ester-3-triuret

Aqueous hydrolysis

methyl-2-(4-methoxy-6-methyl-1,3, 5-triazin-2-yl-amino)-3-thiophene-carboxylate (Ref: IN-D8856)

Aquous photolysis

4-amino-6-methyoxy-1,3,5-triazine-2-methanol (Ref: IN-L9622)

Poultry

methyl-3-sulfo-2-thiophene carboxylic acid (Ref: IN-T700)

Poultry

4-amino-6-methyl-1,3,5-triazin-2-ol (Ref: IN-B5528)

Soil; Plants

3-sulfo-2-thiophenecarboxylic acid (Ref: IN-N9134)

Sediment (anaerobic); Plants

N-(4-hydroxy-6-methyl-1,3-5-triazine-2-yl)-urea (Ref: IN-31804)

Plants

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

0.8

Low potential

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 100

Rat

Moderate

(ppm diet)

> 2200

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

> 175

Unknown species Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2510

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5620 mg kg feed⁻¹

Anas platyrhynchos

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

Colinus virginianus NOAEL

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 56.4

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

> 250

Oncorhynchus mykiss

Low

Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

60.7

Daphnia magna

Moderate

Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

100

Daphnia magna

Low

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

0.0013

Lemna gibba

High

Non-target plants

0.606

Beta vulgaris
Vegetative vigour, ER₅₀
as g ha⁻¹

0.613

Beta vulgaris
Seedling emergence, ER₅₀
as g ha⁻¹

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

> 0.8

Pseudokirchneriella subcapitata 72 hour ErC50

Moderate

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 100

Apis mellifera

Low

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 7.1

Apis mellifera

Moderate

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Bumblebees (Bombus spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Mason bees (Osmia spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Other pollinators (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other pollinators (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

> 2000

Eisenia foetida

Low

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

34.3

Eisenia foetida

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

450

>; Mortality, as g product ha⁻¹ (50 SC: conc 500 g l⁻¹)
Aphidius rhopalosiphi

% Effect

Mortality [Dose: 0.082 kg ha⁻¹]
Aphidius rhopalosiphi adult

Other arthropod (2)

LR₅₀ g ha⁻¹

450

>; Mortality, as g product ha⁻¹ (50 SC: conc 500 g l⁻¹)
Typhlodromus pyri

% Effect

4.6

Mortality [Dose: 0.082 kg ha⁻¹]
Typhlodromus pyri protonymph

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect

Dose: 0.4 kg ha⁻¹

Mesocosm study data

NOEAEC mg l⁻¹

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.03

Rat 4 hr

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

0.02

Rat SF=100

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

None allocated

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

0.15

Rat SF=100

Dermal penetration studies (%)

0.6-6.4

concentration and formulation dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risks to bystanders identified

Occupational

No unacceptable risks to operators or other workers identified

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

May decrease bodyweight

Handling issues

Property

Value and interpretation

General

IMDG Transport Code is usually 9
Not explosive or oxidising

CLP classification 2013

Environment: H400, H410

EC Risk Classification

N - Dangerous for the environment: R50, R53

EC Safety Classification

S60, S61

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Usually 3077

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

thifensulfuron-methyl

French

thifensulfuron-methyle

German

Thifensulfuron

Danish

thifensulfuron-methyl

Italian

tifensulfuron-metile

Spanish

tifensulfuron-metil

Greek

thifensulfuron-methyl

Polish

tifensulfuron metylu

Swedish

tifensulfuronmetyl

Hungarian

tifenszulfuron-metil

Dutch

thifensulfuron-methyl

Record last updated:	21/10/2020
Contact:	aeru@herts.ac.uk
Please cite as:	Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242